IE34441B1 - Dibenzazepine derivatives and their preparation - Google Patents

Abstract

1301366 Dibenzazepine derivatives RHONEPOULENC SA 7 Aug 1970 [7 Aug 1969] 38279/70 Heading C2C Novel compounds I: (in which each of R and R<SP>1</SP> is H, C 1-5 alkyl, C 1-5 hydroxyalkyl, hydroxyalkoxyalkyl of 1-5 carbon atoms in each alkyl residue, or phenyl-C 1-5 alkyl optionally substituted in the phenyl nucleus by one or more of halogen, C 1-5 alkyl, C 1-5 alkoxy, NH 2 or CF 3 , R 1 is H or C 1-5 alkyl and one of the symbols X is Cl and the other symbols X are each H) and acid addition salts and quaternary ammonium derivatives thereof, are prepared by (a) reducing a compound II: or (b) reducing a compound III: (in which CH 2 R 2 has the same meaning as R<SP>1</SP> and R<SP>3</SP> is H, C 1-5 alkyl or phenyl-C 1-5 alkyl optionally substituted by one or more of halogen, C 1-5 alkyl, C 1-5 alkoxy or CF 3 ), or (c) reacting a compound IV: with a compound of formula R 2 CHO, or (d) reacting a compound V: (in which Ac is acyl) with a compound of formula R 2 CHO, and removing the acyl group in the resulting product by hydrolysis, or (e) reacting a compound IV with a compound of formula R 4 -Z (in which R 4 has the same meaning as R<SP>1</SP> but is not H, and Z is a reactive ester residue) or (f) replacing the radical Y in a compound VI: (in which Y is CN, alkoxycarbonyl, alkanoyl alkanesulphonyl or arylsulphonyl) by a hydrogen atom, or (g) reducing a compound VII: (in which R 5 is H or C 1-5 alkyl and R 6 is C 1-5 alkyl), and, if desired, converting a resulting compound into an acid addition salt or quaternary ammonium derivative. Compounds II are prepared by reacting a compound C: with hydroxylamine. Compounds X and intermediates therefor are prepared by the following reacting schemes A and B: Compounds III are prepared by acylation of com unds VIII: 2 - Chloro - 5 - methyl - 10 - ethoxycarbonylamino - 10,11 - dihydro - dibenzo[b,f]azepine is prepared by reacting ethyl chloroformate with 2 - chloro - 5 - methyl - 10 - amino - 10,11 - dihydrodibenzo[b,f]azepine. Pharmaceutical compositions for oral, rectal, parenteral or topical administration, comprise a compound I or a non-toxic acid addition salt or quaternary ammonium derivative thereof, together with a pharmaceutical carrier. The active ingredients have antidepressant, analgesic, anticonvulsive and tranquillizing activity. [GB1301366A]